Azodyestuffs insoluble in water and process of making same



l aten ted Aug. 25, 1931 UNITED ST T FFHCEQ ARTHUR ZITSCI-IER, or orrnNBAcH-ou-rnE-MAIN, AND ROBERT SOI-IMITT, or DARM- s'rnnr, GERMANY, ASSIGNORS TO GENERAL ANILINE woRKs, rim, on NEW YORK,

' N. Y; CORPORATION OF DELAWARE AZODYESTUFFS INSOL'UBLE IN WATER AND PROCESS OF MAKING SAME No Drawing.fiipp1ication filed April 3, 1329, Serial No. 352 .318, and in Germany April 7 1928.

HJ A naphthalene The dihydroxy quinoline compounds used in our process may be prepared for instance in an analogous manner as descrlbed 1n Berichte der Deutschen Chem1sohen Gesellschaft, vol.

60, page 832 or 1108, or in Camps Archiv der Pharmazie, vol. 287, page 659.-

\Vhereas QA-dihydroxy quinoline itself yields useless dyeings when employed for the'manufacture of ice-colors according to our process Valuable pigment dyestuffs are obtained by means of the usual substrata, or fast dyeings and printings on the' fiber. by producing the dyestuffs according to the icecolor method. In consequence of the substantive properties of these combining components the goods padded therewith may be developed without being previously dried. H In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in centigrade degrees, but it may be understood that our invention is not limited to the j particular products or conditions of reaction mentioned therein.

Example Cotton yarn Well boiled and dried is padded with a solution containing per liter l0 grs. of 7.8-benzo-2. l'dihydroiiy-quinoline of the probable formula:

H-M so 56" (prepared from l-naphthylamlne and malonic ester in an analogous manner as detaining per liter 1.62 grs. of 2.5-dichloro aniline. Thereafter it is rinsed, soaped and dried.

In'this manner a brownish-orange dyeing of a very good fastness is obtained.

The following table shows the shades of dyeings prepared in like manner from the same padding solution and from the diazo compounds of the following bases:

Base Shade 1-amino-anthraquinone h Brownish yellow-orange. o-amlno-azo-toluene Yellowish-red.

Cotton yarn previously treated in a suitable manner is padded with a solution con-' taining per liter l0 grs. of 5.6-benzo-2/1-dihydroXy-quinoline of the probable formula:

(light yellowish needles melting above 345, prepared from 2-naphthylamine and malonic ester in an analogous manner as described in Berichte der Deutschen Chemischen Gesellschaft, vol. 60, page 832), 15 ccm. of a caustic soda solution of 34 B.,-1O com. of Turkey red oil and 28 grs. of Glaubers salt. Then it is well wrung out and developed with a diazo solution partially neutralized with sodium acetate and containing per liter 1.62 grs. of 2.5dichloro aniline. Thereafter it is rinsed, soaped and dried.

In this manner an orange-yellow dyeing of a very good fastness is obtained.

The following table shows the shade of dyeings prepared in like manner from the same padding solution and from the diazo compounds of the following bases:

Base Shade 5-nitro-2-amino-toluene Reddish-oran'ge. l-aminoanthraquinone Yellowish-orange.

Example 3 I taining per liter 10 grs. of 6.7-benzo-2.4-dihydroXy-quinolineof the probable formula:

solution partially neutralized with sodium acetate and containing per liter 1.62 gm. of 2.5-dichloroaniline. Thereafter it 1s rinsed, soaped and dried.

In this manner an orange-yellow dyeing of a very good fastness is obtained.

The following table shows the shades of dyeings prepared in like manner from the same padding solution and from the drawcompounds of the following bases:

Base Shade Yellowish-orange Brownish-orange Brownishorange Yellowish-red 2-amino-diph enyletlier 5 nitro-2-a-mino-to1uene l-amino-anthraquinone o-amino-azo-toluene Leanna;

line compound of the probable general formu- HQGCV ndpbtialene 2. A process which eomprims combining a diazo'tized compound not containing sulfonic orcarboxylicgroups with 6.7-benzo&2.4 dihydroxy-quinoline of the probable formula:

, Ibo/L 3..As new compounds the azotlyestufls: of the probable germ-ml formula:

aryI'-N N--G wherein the arylgroup 'may contain further azo-groups, which compounds are colored powders, lnsoluble in water yielding valuable color lakes or when produced on the fiber fast dyeings and printings.

4. As new compounds the azodyestuffsof the probable general formula on wherein the. arylgroup may contain further azo-groups', which compounds are colored powders, lnsoluble in water yielding valuable color lakes or when produced? on the fi b'erfas't dyel'n'g's' and prfnt'i'ngs; y

In testimony whereof, I afiix m1 1 nature.

'- ARTHUR- zirgo ER.

testimony ROBERT SCHMITTi 

